My Sissy journey - Sex Stories

My Sissy journey

... head down. When he was done with my throat, he pulled me by the arm to a table that belonged to the parking lot and threw me on my back.

He pushed my panties aside, spit on my greedy hole and slowly pushed his huge dick into me with its full length. I had never felt anything so fucking good. Overwhelmed by my horniness, my brain virtually shut down. He owned me completely. When he got a little faster and harder, choking me a little, I had my first hands-free orgasm. Completely unimpressed, he continued while my moans grew louder and louder. I noticed how he was getting closer to his climax. Just before he pulled out his cock he stripped off the condom and came all over my body. The load was huge. I immediately set about licking him clean, a little sad that it was already over after about 15 minutes.

My disappointment quickly turned when I saw him take a new condom out of his pocket and slip it on. He brought me rudely back to my feet and bent me forward over the table. Before my brain reacted he was already fucking me again. This time even harder as he held my hands on my back to get momentum. Only a few seconds later I came again. After another 20 minutes of pounding he was close to orgasm again, this time cuming on my ass and the back of my dress. And again I set about licking his dick clean.

He forced me to suck his cock again until he blasted another load all over my mask. Never before had I seen someone cum three times in a row and especially not with such a ...

... amount of cum. When I was about to leave he held me tight and ordered me to walk a big round through the nearby town and offer my services to everyone I meet. So off I went with loads of sperm on the mask, the wetlook dress, the stockings and very wobbly on my legs. Fortunately (or unfortunately) I met but no one.

Back at the parking lot, he pressed $5 into my hand and told me I wasn't worth more and disappeared. I liked that a lot for some reason and went home satisfied. The next day I got a message with: Test passed. Seconds later he introduced himself as Mike and told me he will message me again.

During all that time, I led a double life, so to speak. I lived normally as a man, went to work, even had a girlfriend. My girlfriend worked in shifts, so I often had time for meetings.

In the days after the meeting with Mike, to my amazement, even a dominatrix had contacted me, who wanted to have me as her property. Desperate and submissive as I was I agreed after some chatting. She wanted to prostitute me and keep the money. This excited me very much and I liked to be humiliated.

I also gave my new mistress the contact to Mike to discuss the meeting with the gentlemen round, because I was incapacitated for the time in which I was active as a sissy. A few days later I got a message from my mistress with a time and place. It was the parking lot where Mike had fucked me and at midnight I should be there again. In the meantime I had also bought a penis cage that I wanted to ...